CO5150169A1 - SYNTHESIS OF USEFUL INTERMEDIARIES TO PAREPARATE TRICYCLE COMPOUNDS - Google Patents
SYNTHESIS OF USEFUL INTERMEDIARIES TO PAREPARATE TRICYCLE COMPOUNDSInfo
- Publication number
- CO5150169A1 CO5150169A1 CO99072692A CO99072692A CO5150169A1 CO 5150169 A1 CO5150169 A1 CO 5150169A1 CO 99072692 A CO99072692 A CO 99072692A CO 99072692 A CO99072692 A CO 99072692A CO 5150169 A1 CO5150169 A1 CO 5150169A1
- Authority
- CO
- Colombia
- Prior art keywords
- jpeg
- compound
- formula
- imf
- emi file
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 9
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- 238000004519 manufacturing process Methods 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 150000002466 imines Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 abstract 1
- 229940125715 antihistaminic agent Drugs 0.000 abstract 1
- 239000000739 antihistaminic agent Substances 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
Abstract
Se describe un proceso para preparar un compuesto que tiene la siguiente fórmula:<EMI FILE="99072692_1" ID="1" IMF=JPEG >Donde R, R1, R2, R3 y R4 se seleccionan independientemente del grupo formado por H, Br, CI, F alquilo, alcoxi, dicho proceso comprende:(A) hacer reaccionar un compuesto que tiene la fórmula <EMI FILE="99072692_2" ID="2" IMF=JPEG >donde RA, RB, RC, RD, y RE se seleccionan independientemente del grupo formado por H, halo, alquilo o alcoxi y R5 es arilo o heteroarilo, con un agente deshidratante para producir una imina que tiene la fórmula:<EMI FILE="99072692_3" ID="3" IMF=JPEG >(B) hidrolizar la imina producida en el paso (A) para producir el compuesto que tiene la fórmula (I). También se describe un proceso para preparar un compuesto que tiene la siguiente fórmula:<EMI FILE="99072692_4" ID="4" IMF=JPEG >Donde RA, RB, RC, RD y RE se seleccionan independientemente del grupo formado por H, halo, alquilo, o alcoxi y R5 es arilo o heteroarilo. También se describe un proceso para preparar un compuesto con la siguiente fórmula:<EMI FILE="99072692_5" ID="5" IMF=JPEG >que comprende:hacer reaccionar un compuesto que tiene la fórmula:<EMI FILE="99072692_6" ID="6" IMF=JPEG >con NH2R5 en la presencia de un catalizador de paladio, monóxido de carbono, una base y un éter seleccionado del grupo formado por:CH3OCH2CH2OCH3; CH3OCH2CH2OCH2CH2OCH3;CH3OCH2CH2OCH2CH2OCH2CH2OCH3, donde X es H, Br, CI, o F y R5 es arilo o heteroarilo. Los compuestos preparados por medio de estos procesos son útiles como intermediarios para preparar compuestos que son antihistaminas o inhibidores de farnesil transferasa de proteína.A process for preparing a compound having the following formula is described: <EMI FILE = "99072692_1" ID = "1" MFI = JPEG> Where R, R1, R2, R3 and R4 are independently selected from the group consisting of H, Br , CI, F alkyl, alkoxy, said process comprises: (A) reacting a compound having the formula <EMI FILE = "99072692_2" ID = "2" IMF = JPEG> where RA, RB, RC, RD, and RE they are independently selected from the group consisting of H, halo, alkyl or alkoxy and R5 is aryl or heteroaryl, with a dehydrating agent to produce an imine having the formula: <EMI FILE = "99072692_3" ID = "3" IMF = JPEG> (B) hydrolyze the imine produced in step (A) to produce the compound having the formula (I). A process for preparing a compound having the following formula is also described: <EMI FILE = "99072692_4" ID = "4" IMF = JPEG> Where RA, RB, RC, RD and RE are independently selected from the group consisting of H, halo, alkyl, or alkoxy and R5 is aryl or heteroaryl. A process for preparing a compound with the following formula is also described: <EMI FILE = "99072692_5" ID = "5" MFI = JPEG> comprising: reacting a compound having the formula: <EMI FILE = "99072692_6" ID = "6" IMF = JPEG> with NH2R5 in the presence of a palladium catalyst, carbon monoxide, a base and an ether selected from the group consisting of: CH3OCH2CH2OCH3; CH3OCH2CH2OCH2CH2OCH3; CH3OCH2CH2OCH2CH2OCH2CH2OCH3, where X is H, Br, CI, or F and R5 is aryl or heteroaryl. Compounds prepared by these processes are useful as intermediates for preparing compounds that are antihistamines or farnesyl protein transferase inhibitors.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19700398A | 1998-11-20 | 1998-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO5150169A1 true CO5150169A1 (en) | 2002-04-29 |
Family
ID=22727622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO99072692A CO5150169A1 (en) | 1998-11-20 | 1999-11-18 | SYNTHESIS OF USEFUL INTERMEDIARIES TO PAREPARATE TRICYCLE COMPOUNDS |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1131296A2 (en) |
| JP (2) | JP4663122B2 (en) |
| CN (1) | CN1162404C (en) |
| AR (1) | AR028138A1 (en) |
| AU (1) | AU3790200A (en) |
| CA (1) | CA2351693C (en) |
| CO (1) | CO5150169A1 (en) |
| HK (1) | HK1038698A1 (en) |
| MY (1) | MY121795A (en) |
| PE (1) | PE20001243A1 (en) |
| TW (1) | TW509680B (en) |
| WO (1) | WO2000030589A2 (en) |
| ZA (1) | ZA200103246B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1636982A (en) * | 2000-04-18 | 2005-07-13 | 先灵公司 | Synthesis of intermediates useful in preparing tricyclic compounds |
| AU2002368506A1 (en) * | 2002-12-26 | 2004-07-22 | Cadila Healthcare Limited | A process for preparing benzocyclohetapyridin-11-ones |
| CN108218773A (en) * | 2018-02-28 | 2018-06-29 | 朱路英 | A kind of method for preparing resisting allergic rhinitis drug loratadine intermedite |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282233B1 (en) | 1980-06-19 | 2000-09-05 | Schering Corp | Antihistaminic 11-(4-piperidylidene)-5h-benzoÄ5,6Ü-cyclohepta-Ä1,2Ü-pyridines |
| DE3677842D1 (en) * | 1985-05-13 | 1991-04-11 | Schering Corp | METHOD FOR THE PRODUCTION OF PIPERIDYLIDES-DIHYDRODIBENZO (A, D) CYCLOHEPTENES AND THEIR AZODERIVATES, COMPOUNDS MADE THEREOF AND THEIR USE FOR THE PREPARATION OF MEDICINAL PRODUCTS. |
| US4731447A (en) * | 1985-05-13 | 1988-03-15 | Schering Corporation | Process for preparing piperidylidene dihydro-dibenzo(a,d)-cycloheptenes or aza-derivatives thereof |
| US5089496A (en) | 1986-10-31 | 1992-02-18 | Schering Corporation | Benzo[5,6]cycloheptapyridine compounds, compositions and method of treating allergies |
| CA2008878C (en) * | 1989-02-28 | 2003-01-21 | Michelangelo Scalone | Process for preparing pyridine-2-carboxamides |
| US5672750A (en) * | 1994-12-16 | 1997-09-30 | Eastman Chemical Company | Preparation of aromatic amides from carbon monoxide, an amine and an aromatic chloride |
| IL117798A (en) * | 1995-04-07 | 2001-11-25 | Schering Plough Corp | Tricyclic compounds useful for inhibition of g-protein function and for treatment of proliferative diseases and pharmaceutical compositions comprising them |
| BR9612203A (en) | 1995-12-22 | 1999-07-13 | Schering Corp | Tricyclic amides useful for inhibiting g-pro-theine function and for the treatment of proliferative diseases |
| ES2143816T3 (en) * | 1996-05-09 | 2000-05-16 | Lonza Ag | PROCEDURE FOR THE PREPARATION OF ARYLAMIDES FROM HETEROAROMATIC CARBOXYL ACIDS. |
| US5958890A (en) * | 1996-09-13 | 1999-09-28 | Schering Corporation | Tricyclic compounds useful for inhibition of G-protein function and for treatment of proliferative diseases |
| CA2284646C (en) * | 1997-03-25 | 2004-04-06 | Schering Corporation | Synthesis of intermediates useful in preparing tricyclic compounds |
-
1999
- 1999-11-18 AR ARP990105868A patent/AR028138A1/en active IP Right Grant
- 1999-11-18 TW TW088120161A patent/TW509680B/en not_active IP Right Cessation
- 1999-11-18 CA CA002351693A patent/CA2351693C/en not_active Expired - Lifetime
- 1999-11-18 HK HK02100248.8A patent/HK1038698A1/en unknown
- 1999-11-18 WO PCT/US1999/026010 patent/WO2000030589A2/en not_active Ceased
- 1999-11-18 CO CO99072692A patent/CO5150169A1/en unknown
- 1999-11-18 EP EP99972525A patent/EP1131296A2/en not_active Withdrawn
- 1999-11-18 AU AU37902/00A patent/AU3790200A/en not_active Abandoned
- 1999-11-18 CN CNB998135151A patent/CN1162404C/en not_active Expired - Lifetime
- 1999-11-18 JP JP2000583474A patent/JP4663122B2/en not_active Expired - Lifetime
- 1999-11-19 MY MYPI99005048A patent/MY121795A/en unknown
- 1999-11-19 PE PE1999001170A patent/PE20001243A1/en not_active Application Discontinuation
-
2001
- 2001-04-20 ZA ZA200103246A patent/ZA200103246B/en unknown
-
2010
- 2010-03-01 JP JP2010044749A patent/JP2010132701A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2000030589A2 (en) | 2000-06-02 |
| PE20001243A1 (en) | 2000-11-15 |
| JP4663122B2 (en) | 2011-03-30 |
| WO2000030589A3 (en) | 2001-01-04 |
| JP2010132701A (en) | 2010-06-17 |
| MY121795A (en) | 2006-02-28 |
| CA2351693C (en) | 2009-01-20 |
| AR028138A1 (en) | 2003-04-30 |
| ZA200103246B (en) | 2002-07-22 |
| CA2351693A1 (en) | 2000-06-02 |
| HK1038698A1 (en) | 2002-03-28 |
| CN1326444A (en) | 2001-12-12 |
| TW509680B (en) | 2002-11-11 |
| EP1131296A2 (en) | 2001-09-12 |
| JP2002530307A (en) | 2002-09-17 |
| AU3790200A (en) | 2000-06-13 |
| CN1162404C (en) | 2004-08-18 |
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